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After nearly 8 years, I've been debating whether or not it's time. How do I know what's important in deciding whether to leave or stay?

Here are the pros and cons I am taking into account at the moment:

Pros:

  • Flexible schedule
  • Good working conditions & office relations
  • Respected by management
  • Better than average job security.

Cons:

  • Vague job description,
  • Unsatisfying interaction with customers,
  • Organizational issues,
  • Little or no opportunity for advancement,
  • Underpaid (around 10-20%),
  • Only developer in group.

Maybe I have it good and I don't know it, maybe it's crappy compared to other gigs, or typical. What other factors should I be considering to help me make my decision?

When do I know it's time to go?

  • 1
    It worries me for your sake that there's no bullet points about whether you like the actual work. If that's never been a concern, I might play it safe where you're at. – Erik Reppen Jan 19 '14 at 6:51
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Realizing that this is going to sound like one of those general "life advice" answers, and trying to address the universal question in your title, "Is it time to move on?"...

I see a list of pros/cons about the situation in which you work everyday, but what do you feel you're actually lacking?

If your current position gives you comfort and security, then I suspect there's something deeper that you're reaching for in a potential change: a new challenge, something that excites you again, something that pushes you in a direction that you've wanted to explore for a long time, but haven't yet had the change to explore.

Whatever it is, it's deeper than the list of pros/cons you've provided.

As far as the list itself is concerned, none of those things can be addressed by anyone but you. What people want in their jobs is highly individualistic. Try to find the deeper reason(s) you're unhappy and address that instead.

For example (and this is very individual to me), I realized a few years ago what really matters to me.

  • Work - I like to work, and I like to work hard. That doesn't mean going crazy or stretching myself too thing. But I know that what I don't want is a boring, "could do this in my sleep" kind of job.
  • Passion - I have to be doing (or moving toward) a product, company, mission, etc. that I'm passionate about. This one is hard for a lot of people, because even if you work within an industry or position you're passionate about, there will always be "grinding" days where it's going to be work (at least a few). It's also hard to put into words what you really are passionate about, unless you're lucky enough to have known the answer to this for a long time. Cheesy as it might seem, figuring out the passion part is (in my experience) a self-discovery thing you have to do, and sometimes it take years and trying a lot of things that turn out to not be the thing you should spend the rest of your career on.
  • Choice - I figure that working hard, and trying to ever-increasingly work on what I'm passionate about will (I hope) lead to more choice. Choice is ultimately what I want. Choice in my life. Choice in my work (and projects I work on). Choice in my finances (and freedom from having to worry constantly about paying bills). Choice in the long term (e.g. if I take path A vs. B where do I think it'll take me after five years?).

The rest are details and I can't worry about them, because what matters to me are work, passion, and ultimately choice. That's it.

So, the point of all that ranting is this: What's important to you? What are the things that, if you had them (or felt that you were on a road to get them), you wouldn't sweat the details?

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Here are three test factors in which to determine if the current job is for you:

  1. Areas of advancement: The job provides you the ability to enhance or work on your craft. They pay you to attend conferences. There are opportunities to advance onto taking more responsibility and different roles, etc.

  2. Unit cohesion: Your have developed a good sense of unity and cooperative comradeship with your colleagues that it's worth the trouble.

  3. Passion: The job provides you the flexibility to work on what you love most. The job isn't a job. It's your career and you show up to work ready to churn out code or build Acme widgets.

I've left out money / salary / benefits out because if you did your job well and sacrificed yourself and gave it your all your employer would depend on you and salary and benefits shouldn't be a question. You would have the leverage to do what you wanted. Also, money is not always the ultimate factor of if you should keep your job.

Given your situation, if you're even thinking about changing jobs. You probably have to go and start applying. See what the field currently offers and see if it's better for you. Take a couple "sick" days (well i don't recommend it but i've seen it happen) for interviews and see if anyone makes you an offer.

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Looking at this question, I wanted to give a different perspective...

The bottom line is - it's all about you.

I agree with the other posters that work, passion and choice, advancement, cohesion and passion are all reasons that I, personally, would stay or leave a given job. But even more important is how you assess your work and what you see as a plus or a minus. And also by how much you care. And how much better you could or couldn't do in the marketplace right now. You always want the best job (for you) that you can possibly get without too much long term harm to your overall career. Taking those parts part, it's

The best job right now

That's knowing the market and having been in enough recent interviews to know how you rank. I'd advise interviewing and applying to interesting opportunities every few years, just so you know where you rate in the market. Or doing something else that gives you an idea of what your options might be.

Also - scanning job sites and talking to peers will give you an idea of whether those other jobs are really something you'd like - getting the details from someone you trust is always helpful.

Long term career

There's a number of tradeoffs that are awesome in the short term, but perhaps bad in the long term... examples (for me) would be:

  • Job hopping more than every 3 years. I hate change, I don't feel like I really know my job until I've been at it a while, and in my line of work, I look down on people who don't give a new place a decent trial, so I don't want to have a resume with a lot of job changes.
  • Good money, bad challenges - the jobs that pay very good salaries to work on technologies that will be hard to transition to other businesses.
  • Great money, horrible work conditions - I'm thinking of conditions so bad they would affect your long term health.

Note - even these are personal - a person at the end of their career may not care so much about deprecated technologies, particularly if they think there will be a great golden handshake at the end of the work.

Similarly - my metric of 3 years is specific to me... mileage varies.

Best job for you

The most specific of all... many of the cons you mention, I would see as opportunities... so my response is, that these cons are a big deal if you think they are... A lot of your examples come from a weakly structured office that doesn't seem to have much growth or guidance. If you've been working there for 8 years, that's unlikely to change. Some people may see the vagueness you mention as an opportunity to develop their own path. Others will find it debilitatingly frustrating.

I've seen people stick with what I would think of as a lame job for all sorts of personal reasons - and it's hard to argue that family, kids, the commute, or a particular perk is a deciding force that overcomes all sorts of other frustration when figuring out priorities.

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